Palladium-catalyzed C—P bond-forming reactions of aryl nonaflates accelerated by iodide

Mcerlain, H., Riley, L. M. and Sutherland, A. (2021) Palladium-catalyzed C—P bond-forming reactions of aryl nonaflates accelerated by iodide. Journal of Organic Chemistry, 86(23), pp. 17036-17049. (doi: 10.1021/acs.joc.1c02172) (PMID:34726917)

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An iodide-accelerated, palladium-catalyzed C–P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C–P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Riley, Miss Leanne and Sutherland, Professor Andrew and Mcerlain, Miss Holly
Authors: Mcerlain, H., Riley, L. M., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN (Online):1520-6904
Published Online:02 November 2021
Copyright Holders:Copyright © 2021 The Authors
First Published:First published in Journal of Organic Chemistry 86(23): 17036-17049
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
172865EPSRC DTP 16/17 and 17/18Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/N509668/1Research and Innovation Services